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Magazine Chapter 22: Problem 23
Write structural formulas for all the amines of molecular formula \(\mathrm{C}_{4} \mathrm{H}_{11} \mathrm{~N}\). Give an acceptable name for each one, and classify it as a primary, secondary, or tertiary amine.
Short Answer
Expert verified
There are 4 primary, 2 secondary, and 1 tertiary amines for C鈧凥鈧佲倎N.
Step by step solution
01
Introducing Amines and Their Types
Amines are organic compounds characterized by the presence of a nitrogen atom attached to carbon atoms. Amines are classified based on the number of hydrogen atoms replaced by alkyl or aryl groups: Primary (1掳), where the nitrogen is attached to one alkyl group; Secondary (2掳), where the nitrogen is attached to two alkyl groups; and Tertiary (3掳), where the nitrogen is attached to three alkyl groups.
02
Structuring Primary Amines
Primary amines have the formula RNH鈧�, where R is an alkyl group. For C鈧凥鈧佲倎N, potential structures include:
1. Butan-1-amine (CH鈧�(CH鈧�)鈧僋H鈧�)
2. Butan-2-amine (CH鈧僀H鈧侰H(NH鈧�)CH鈧�)
3. 2-Methylpropan-1-amine ((CH鈧�)鈧侰HCH鈧侼H鈧�)
4. 2-Methylpropan-2-amine ((CH鈧�)鈧僀NH鈧�)
These are all primary amines because the nitrogen is bonded to one carbon atom.
03
Formulating Secondary Amines
Secondary amines have the formula R鈧侼H, where R is an alkyl group. For C鈧凥鈧佲倎N, potential structures include:
1. N-Methylpropan-1-amine (CH鈧�(CH鈧�)鈧侼HCH鈧�)
2. N-Ethylethanamine (CH鈧僀H鈧侼HCH鈧侰H鈧�)
These structures are considered secondary amines as the nitrogen is bonded to two carbon atoms.
04
Constructing Tertiary Amines
Tertiary amines have the formula R鈧僋, with three alkyl groups attached to the nitrogen. For C鈧凥鈧佲倎N, the possible tertiary amine is N,N-Dimethylethanamine ((CH鈧�)鈧侼CH鈧侰H鈧�). In this amine, the nitrogen atom is bonded to three carbon atoms, making it a tertiary amine.
05
Summarizing the Amines
1. Primary Amines:
- Butan-1-amine
- Butan-2-amine
- 2-Methylpropan-1-amine
- 2-Methylpropan-2-amine
2. Secondary Amines:
- N-Methylpropan-1-amine
- N-Ethylethanamine
3. Tertiary Amine:
- N,N-Dimethylethanamine
Each amine has different alkyl group arrangements leading to distinct structures and classifications.
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Primary Amines
Primary amines are the simplest type of amines, and they have the general formula \( ext{RNH}_2\) where \( ext{R}\) represents an alkyl group. This means the nitrogen atom is connected to just one carbon atom and two hydrogen atoms. In our case, with the molecular formula \( ext{C}_4 ext{H}_{11} ext{N}\), the primary amines you can form are:
- Butan-1-amine: \( ext{CH}_3( ext{CH}_2)_3 ext{NH}_2\)
- Butan-2-amine: \( ext{CH}_3 ext{CH}_2 ext{CH}( ext{NH}_2) ext{CH}_3\)
- 2-Methylpropan-1-amine: \( ( ext{CH}_3)_2 ext{CHCH}_2 ext{NH}_2\)
- 2-Methylpropan-2-amine: \( ( ext{CH}_3)_3 ext{CNH}_2\)
Secondary Amines
Moving on, secondary amines have the structure \( ext{R}_2 ext{NH}\), meaning two carbon atoms are connected to the nitrogen atom. For our molecular formula \( ext{C}_4 ext{H}_{11} ext{N}\), the secondary amines include:
- N-Methylpropan-1-amine: \( ext{CH}_3( ext{CH}_2)_2 ext{NHCH}_3 \)
- N-Ethylethanamine: \( ext{CH}_3 ext{CH}_2 ext{NHCH}_2 ext{CH}_3 \)
Tertiary Amines
Tertiary amines expand on this concept with the formula \( ext{R}_3 ext{N}\), which implies the nitrogen is bonded to three carbon atoms, albeit not necessarily to three different ones. For our formula \( ext{C}_4 ext{H}_{11} ext{N}\), the tertiary amine is:
- N,N-Dimethylethanamine: \( ( ext{CH}_3)_2 ext{NCH}_2 ext{CH}_3 \)
Structural Formulas
Understanding the structural formulas of amines is key to identifying their properties and reactivity. Structural formulas depict how atoms in a compound are laid out. For amines, this involves arranging carbon atoms such that they align with the nitrogen appropriately as primary, secondary, or tertiary.
- In Butan-1-amine, the nitrogen atom is connected to the end of a straight carbon chain.
- In 2-Methylpropan-1-amine, the nitrogen is on a branched chain.
- N-Methylpropan-1-amine shows N joined to a methyl group.
- N,N-Dimethylethanamine has a nitrogen linked to two methyl groups.
IUPAC Naming in Organic Chemistry
In organic chemistry, the IUPAC naming method provides a systematic way of naming chemical substances, ensuring each compound has a unique name. For amines:
- Primary amines are named by taking the name of the alkyl group and adding "-amine," such as "butan-1-amine."
- Secondary amines feature the "N-" prefix to denote the attached groups, like "N-methylpropan-1-amine."
- Tertiary amines are named similarly, with "N,N-" prefixes if two identical groups are attached to the nitrogen, such as in "N,N-dimethylethanamine."
